Sodium hydride → HCID 53650858, compound

HRID 864752Notes

Reaction equation

HRID 864752 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.[H][H].Cl[C:15]1[C:20]([Cl:21])=[CH:19][C:18]([Cl:22])=[CH:17][N:16]=1>C1COCC1>[Cl:21][C:20]1[C:15]([O:3][CH2:4][CH2:5][N:6]2[CH2:11][CH2:10][O:9][CH2:8][CH2:7]2)=[N:16][CH:17]=[C:18]([Cl:22])[CH:19]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 27666Pyridine, 2,3,5-trichloro-HCID 611632-MorpholinoethanolHCID 178418361HCID 178418361, compound

Product 1

HCID 53650858HCID 53650858, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

97% sodium hydride (2.72 g. 0.11 mol) was suspended in THF (100 ml) under nitrogen and a solution of N-(2-hydroxyethyl)morpholine (14.4 g, 0.11 mol) in THF (15 ml) was added in portions. When hydrogen evolution had ceased, a solution of 2,3,5-trichloropyridine (18.2 g, 0.10 mol) in THF (25 ml) was added at such a rate as to maintain a gentle reflux. The reaction mixture was refluxed for 2 hours and the solvent was subsequently removed in vacuo. The residue was taken up in water/CH2Cl2, the organic layer was separated and the solvent was removed in vacuo to afford 26.3 g (94.9%) of 3.5-dichloro-2-[2-(4-morpholinyl]ethoxy]pyridine as a crystalline solid.

Workup

  1. temperatureto maintain a gentle reflux
  2. temperatureThe reaction mixture was refluxed for 2 hours
  3. customthe solvent was subsequently removed in vacuo
  4. customthe organic layer was separated
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e3eda8b73cd4483baf3d2a07bba1b29e
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Reaction notes

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